... I have a remote host running Parity which I can connect to via an SSH Tunnel. I've forwarded ports 8180, 8546 and 8646 through the tunnel to the computer running Parity.
I can load the UI for that Parity instance from any other computer on my LAN (after I make a SSH connection to that computer). My parity chrome extension is also working and able to connect to the host's parity instance.

Now, let's say I want to use my NanoS to sign transactions from a computer on my LAN (other than from the computer where Parity is actually running).. I'd like to be able to connect the Nano to the computer I'm using at the time and have Parity "see" it. As far as I can tell, Parity is not seeing it.

When the Parity Signer pops up while using EtherDelta (for example), it tells me to connect the hardware wallet before confirming the transaction and the confirm button is grayed out. So it seems like I'd need to connect the Nano to the server actually running Parity.

1 Answer
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I am able to remotely mount a local USB device to a remote Parity host. I have not tested it with an intermediary SSH tunnel, but it may be possible with SSH port forwarding with appropriate ports forwarded. This method may require a substantial rework of your infrastructure.

I have installed Parity on a Ubuntu server 16 LTS guest VM on a VMware ESXi 6.5 hypervisor host. The VM runs in a separate subnet, distinct from my (macOS Sierra) workstations subnet. A pfSense firewall guest VM separates the two subnets, providing routing and filtering. I typically use SSH port forwarding from my workstation to remotely browse my Parity wallet on the Ubuntu host VM.

I am able from my workstation to use VMware Fusion Pro 10.1.1 to connect to the ESXi host and attach a local USB device to the remote Ubuntu host VM.

It should be noted that my workstation has direct connectivity with the ESXi host, and thus an SSH tunnel is not required to connect my workstation to the ESXi host. I expect it would be possible to remotely connect VM Fusion Pro (or VMware Workstation) to an ESXi host over an SSH (port forward) tunnel, if necessary.